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Asymmetric Iminium Ion Catalysis: An Efficient Enantioselective Synthesis of Pyranonaphthoquinones and β‐Lapachones
Author(s) -
Rueping Magnus,
Sugiono Erli,
Merino Estíbaliz
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705110
Subject(s) - enantioselective synthesis , iminium , chemistry , trimethylsilyl , organocatalysis , lewis acids and bases , catalysis , combinatorial chemistry , organic chemistry
An addition–cyclization reaction cascade triggered by an organocatalyst was used for the enantioselective preparation of a series of biologically active 1,2‐ and 1,4‐pyranonaphthoquinones from aliphatic and aromatic α,β‐unsaturated aldehydes and 2‐hydroxy‐1‐4‐naphthoquinone. A trimethylsilyl‐protected diarylprolinol serves as the Lewis base organocatalyst.